In Flames
by Tracy Space Cowgirl
Summary: Yale is Sam's college choice. In his Junior year, Sam meets the one girl who will change his world, and break his heart. Alternate Universe, Crossover with Gilmore Girls. Sam Rory Pairing.


In Flames  
by Tracy  
Rating: PG-13  
Pairing: Sam Winchester/Rory Gilmore  
Summary: Yale is Sam's college choice. In his Junior year, Sam meets the one girl who will change his world, and break his heart. (Alternate Universe)  
Spoilers: For the 4th, 5th, and 6th seasons of Gilmore Girls in particular. Spoilers for Pilot of Supernatural.  
Disclaimer: I don't own Gilmore Girls or Supernatural, naturally. I just own an abnormal need to pair the Winchester brothers with girls on the WB shows that the actors portraying them used to appear on. It's a sickness, I think. But a FUN sickness.

* * *

Sam had all but decided that Stanford was definitely the college for him, when he received an acceptance letter in the mail from Yale. An acceptance from an Ivy League college? Sam couldn't believe it. 

An acceptance to an Ivy League college meant little to John Winchester, as did the full ride scholarship that followed a couple of weeks later.

But hell, if he was going to rebel against his father, Sam decided that he would do it in style. And so Sam Winchester became a member of the Yale Class of 2005.

New Haven, Connecticut was a long way from Kansas. It took Sam a little while to get used to college life, but he took to school as a duck takes to water. He excelled in his classes, landing on the Dean's list each semester. He joined the staff of the Yale Daily News, figuring that having an extracurricular couldn't hurt. Writing articles was easy- he'd been writing case reports for his Dad since fourth grade. If he could make that exciting, he could take anything the editor threw at him.

Sam was popular. That, in itself was a new experience for him. He'd never quite stayed in one school long enough to make many friends- John had moved the family almost every year, if not every school semester. For the first time, Sam was free from his brother's shadow. At Yale, Sam's friends were his friends because they wanted to be around him, not his charismatic older brother. He dated, but casually, nothing serious or steady. Sam didn't have piles of money like many of his well to do classmates, but a work study job at the library helped him get by. He'd even been invited to join "The Life and Death Brigade", a ultra-exclusive secret society, but had turned them down, figuring that he already had way too many secrets to keep.

During Sam's Junior year of college, everything changed.

Rory came into his life.

That year, he accepted a job as a freshman councillor- meaning that he'd live in Durfee dorm with a bunch of freshmen boys, and act as a mentor. Tess, the first floor girl's councillor had a family emergency and had to go out of town that night- and she'd asked him and a couple others to check in on her girls. Sam was dutifully patrolling the first floor hallway when he'd noticed quite a commotion coming from one suite. A bunch of giggling girls ran out, and Sam snuck in the door.

The suite was awash with freshmen girls, in different groups, eating a massive variety of food.

"Woo, check this one out!" One red head hooted, as she looked in Sam's direction.

Sam blushed, and figured that although abnormal, there wasn't anything wrong with a bunch of freshmen having a party their first night at college. Hell, his freshman year, Logan Huntzberger had brought booze to the party, and that little get together had gotten completely out of hand. This didn't look anywhere near as dangerous as that fiasco.

He had turned around to leave when he felt a thin pair of arms wrap themselves around his midsection. Shocked beyond belief, he turned around.

"Dean! What are you doing here?" The attractive brunette wrapped around his exclaimed. "Did you come to see me? Or did you get in on late acceptance or something? And what about Lindsay?"

"Um….Dean's my brother." He stuttered, at a loss for what to say.

"He is?" She shrunk away from him. "He never mentioned having a brother."

"We don't talk much." Sam shrugged, wondering just what his Casanova of a brother had been up to, corrupting young girls in Connecticut. Of all the stupid things…

"Oh." She replied, a blush rising over her face. "Yeah. Well, if you do happen to say hi to him, tell him that Rory Gilmore said hi, okay?"

"Will do." He stuck out his hand to shake hers, and marvelled at how her tiny hand seemed to fit his. "I'm Sam. I'm the second floor boy's councillor here at Durfee. Nice to meet you."

"Nice to meet you, too, Sam Forrester."

He chuckled. "Sam Winchester's my name."

"You're not Dean Forrester's older brother?"

"Not quite. I'm Dean Winchester's little brother."

"Wow. I mean…" Rory's blushed deeper. "You look remarkably like my ex-boyfriend. Remarkably."

Sam breathed a small sigh of relief. So Dean hadn't been corrupting Connecticut's young women. Yet.

"Dean, what are you doing here?" A woman, somewhat old to be a college freshman remarked, walking up to them.

"This is, um, Sam. Sam Winchester. He's the boy's councillor here, and believe it or not, he's not at all related to Dean. I mean our Dean, because actually he has a brother named Dean." Rory babbled. "And Sam, this is my Mom…Lorelai."

"Oh. Nice to meet you." Lorelai nodded. "Talk about your Patty Duke Déjà vu moment, huh?"

"Well a hotdog certainly does make Patty loose control." Sam laughed.

"He gets our inane pop culture references." Lorelai nudged Rory in the ribs. "See, Yale does breed genius!"

"He's a regular rocket scientist!" Rory said in a small voice.

"So, Sam, you've been here at Yale for awhile, right?"

"I'm a Junior, actually."

"Great." Lorelai paused slightly. "So I'm guessing that you have a pretty good idea about what take out is edible in this area?"

"Yeah. I guess."

"Perfect!" Lorelai exclaimed. "Follow me, Pinky, and I will show you how we're trying to take over the world tonight…"

* * *

That night was the beginning of Sam's induction into the Gilmore Family. 

Two weeks later, he received a care package from Lorelai. It was filled with ramen soup, Mallow mars, a bag of roast coffee (with a post-it- note explaining that this came from Luke's- which served the best damn java in Stars Hollow, if not the world), and a few candy bars. The simple gesture touched Sam incredibly. It was the first care package he'd ever gotten.

It was easy to become friends with Rory; they shared a love for talking back at cheesy, bad, movies, and reading. They had movie nights together, along with one of the guys on his floor who Rory had also befriended- a guy who had the unfortunate experience of waking up naked on the first floor after the first big dorm party- which led to Marty getting the unfortunate nickname of "Naked Guy". Sam ran into Rory often in the library, and they'd swap commentary on different books that they'd read.

Sam met Rory's grandparents at the Yale Harvard game, when Lorelai spotted him walking by the Gilmore's tailgate party, and drug him over. The elder Gilmores were…a bit much, but nothing compared to the Banshees of Wala Wala, Washington that he'd fought four years earlier with Dean.

Besides, he kind of liked being part of a family. John and Dean were Sam's family, but they were dysfunctional at best. And though the Gilmores weren't exactly normal, they were a hell of a lot more cohesive than the Winchesters were. And being around Lorelai made Sam dream of what it would have been like if his mother lived. If Mary was alive, she would have drug John and Dean across the country to visit Sam and see a football game. He knew she would have.

And when Rory found out that Sam had nowhere to go that Christmas, and was planning on spending the holiday holed up in a hotel room by himself, she insisted that he come home to Stars Hollow with her. He slept on the Gilmore's couch, but it was, by far the merriest of Christmases that Sam could recall. Stars Hollow was like a dream, a sleepy little town where everyone knew your name, and practically everything about you. They were wacky but caring, and there was always something going on. It was about as close to heaven as Sam could imagine.

During the Spring Semester, Sam spent more and more time around Rory. They worked together on the Yale Daily News, and had study sessions together in the library. Sam's respect for Rory grew as he spent more and more time around her neurotic roommate, Paris Gellar. He even went home with Rory a couple of weekends, and helped the construction crew at her mother's inn. While they were there, he met Dean Forrester, his supposed doppelganger, though personally, he couldn't see how they looked alike at all.

Sam drove Rory to her great-grandmother's funeral- it was the least he could do. Rory called him while she was on spring break, and left what seemed to be a drunken dare babble on his voice mail. There was no doubt about it, they were growing closer.

When he abandoned his books in the middle of studying for his last killer final to rescue Rory from a blind date via Emily gone bad, Sam realized that he had fallen for Rory. He'd never had feelings like this, feelings so strong for a girl like this before. She was beautiful, and smart, and...

He couldn't date her, certainly, while she was living in the dorm where he worked, right? Wasn't it a conflict of interest or something like that ? He accompanied Rory back to her dorm, about to say something to her, damn it all, the school year was ending and Rory wouldn't live in the Freshman dorms next year- only to find that one of her ex-boyfriends was waiting for her at the door. Sam left in a hurry.

It was awkward being near her at the test run of the Dragonfly Inn, which Lorelai had insisted he attend. Late that night, after most everyone had turned in for the night, he sat with Rory out in back of the Dragonfly, staring up at the stars from a flannel blanket.

"So…how was…your boyfriend?" He asked softly.

"Jess? I'm not dating him." Rory shook her head. "He showed up, unannounced, at my dorm room, and just expects me to drop…my life to run away to God knows where with him. Who would actually do that?"

"So…you're not…"

"Nope. Not." Rory said with a shrug. "I'm still one of those dangerous, crazy, swinging singles."

Sam's heart swelled at the news. She wasn't…no strings were attached to Rory. His joy outweighed his anxiety, and he leaned over and kissed Rory.

She kissed him back.

They made out under a starlight sky. Rory was lying underneath him on the blanket when Kirk ran out of the Inn, stark naked, with an irate Luke in tow.

Later, they'd discover that this was Kirk's second nude midnight romp, as his first trip had messed up Lorelai and Luke's first embrace.

Sam was pretty sure that Kirk had to be at least part demon.

* * *

His Senior year at Yale was Sam's best yet. 

He spent more time in Rory and Paris' dorm room than his own. Sam and Rory were going steady now, and they had been for the entire summer. Sam had never been happier than he was, waking up in the morning with Rory in his arms. They were almost constantly together, save work and class. Often, Sam would go home with Rory on the weekends. They double dated with Luke and Lorelai, or Rory's best friend Lane and her boyfriend Lane. Sam even went to Friday Night Dinners.

Richard and Emily accepted him, which was a hell of a lot more than they did for poor Luke. Sam was a Yale student, with excellent grades, who was planning to go to law school- that seemed to be enough to fit their plans for their granddaughter. Sam tried to run interference for Luke when he could, joining Richard and Luke for golf, although he had absolutely no idea what he was doing.

Sam wanted to throttle Logan Huntzberger as he flirted with Rory. She was gone all weekend on a "Life and Death Brigade" event, getting notes for an article, and Sam was livid. He waited in her dorm room with a dozen red roses, and Rory had assured him, with words and actions, that there was no one else in her heart.

Sam was an usher at Richard and Emily's vow renewal. He daydreamed during the ceremony, wondering what it would be like to marry Rory.

When Lorelai and Luke broke up, he broke the speed limit to get Rory home to her mother. While Rory soothed the crushed Lorelai, Sam cleaned the house and cooked. He fixed the light bulbs he knew Lorelai couldn't reach, because it was something he could do. It was something, to see Stars Hollow decked out in pink and blue ribbons. Sam wore a pink one when Taylor insisted he choose, but he didn't feel right picking either.

Along with Sookie and Michel, he helped paint Lorelai's garage a funky color of pink.

The dreams started just about the same time that Luke and Lorelai reconciled. Sam dreamed of Rory, engulfed in flame. The dreams were so insistent, and so similar to his father's story of Sam's mother's death, that Sam broke down and emailed his brother, asking Dean to recall the familiar tale. They matched exactly.

Sam broke up with her after graduation.

It should have been the happiest day of his life.

He'd even toyed with the idea of proposing to Rory, though obviously they wouldn't get married until after she finished school. Instead of getting down on one knee, Sam gave her lame excuses and broke her heart.

Sam drove to his off campus apartment, which Rory had helped decorate, with tears in his eyes.

Dean was there waiting for him. Not to congradulate his Sam on graduation, but to enlist him on a mission to find their missing father.

Sam agreed. What did New Haven hold for him without Rory? He couldn't have a normal life, could he? Sam had always had visions, but lately, they became clearer and stronger. He was being called to the very life he tried to escape.

Months later, they passed through New Haven, after a case fighting the New Jersey Devil. Sam saw Rory through the windows of the Impala, on the arm of Logan Huntzberger.

He wanted to jump out of the car and punch Logan out, but Sam knew he had no right.

Nothing good in his life had ever stayed. It either went away, or dissolved, like his mother in flames.


End file.
